In 2009, Eric Daigh was your typical multimedia designer. He worked on album covers. Websites. Pretty much anything you could build and sell with an Adobe product. But that year, he won an art contest in his home state of Michigan, submitting a portrait he’d made for his wife’s anniversary. Instead of ink or paint, it used pushpins.

A few years later, Daigh spends about half of his waking hours creating custom commissioned pushpin portraits for some of the biggest brands in the world, like Acura and 3M, while making his way into both the Guinness Book of World Records and Ripley’s Believe It Or Not. He has no formal training in physical art. But you could say that the business is in his blood.

"My father is a painter, so that was always a viable path. Where he made money was he was as an illustrator back when that was a thing you could be," Daigh tells me. "And then he brought home the first Mac in 1989, and all his colleagues had told him this is the future. But being a draftsman, he had no idea how to make the thing work. That’s where I entered. I was about 12 or 13, so I tore into it because it was a computer and it was fun. There were games on it.

"Then he sort of asked me, ‘So long as you’re going to spend all this time on the computer, could you open QuarkXPress and figure that out?’ We sort of worked together. And that was the beginning of me working in design. I was young enough it was a real novelty to be helping my dad to use his job. To my dad, it was a useful novelty to have his son helping him do his job."

Daigh renders a paint-by-numbers grid.

About 20 years later, Daigh would become restless in his digital world, craving the satisfaction of creating something analog.

"You do anything for too long, and you want something to be the other. The opposite of the digital work I was doing was tangible," he explains. "I’d painted along the way, but nothing ever that was all that interesting to me. Then I tried this experiment with this picture of my little brother, still staying true to pixels which I was very comfortable with."

That experiment turned into a rocket for Daigh’s career. Using software, he simplified a photo of his brother into just five colors, creating an image that’s essentially a very large thumbnail. With the pre-mapped color grid in-hand, Daigh placed correlating pushpins in each spot, recreating this low-fidelity image into a reimagined pointillism. "It worked to a degree that it was interesting, or a conversation piece," Daigh explains, which was just enough for him to stick with it and hone the technique.

That technique led to the portrait of his wife, which led to winning an art show, which led to putting some pieces up in a gallery, which led to his first sale.

Now, Daigh has his pushpin mosaics down to a science. He photographs his own portrait, runs it through a software conversion process that creates (red, yellow, blue, black, and white) dots and then he examines it at the pixel level for algorithmic abnormalities, which he’s gotten very, very good at spotting. Whereas the human eye will want a shadow to contain a smooth gradient of color—maybe blue to black—computers tend to render these blocks out into distracting patterns that need to be hand-smoothed.

Finished portrait, Ben Silbermann.

"What’s interesting is how easy it all is to fail. The images just look like shit when you begin—and that’s to be expected. You’re asking the image to be this really obtuse thing, and it’s really not supposed to work," Daigh explains. "But what’s fun is it’s set up to fail, yet you’re able to nudge it along, put bandaids here or there, and get to the point that the portrait works."

While most artists will go on about "inspiration" or "vision," Daigh’s view of his work is far more practical. He considers his job to be "problem solving," and in that regard, he sees the role of an artist as parallel to that of a parent, teacher, politician, or engineer … well, almost.

"If you’re an engineer, you have a finite goal you’re trying to pull off. If you’re an artist, the landscape is always shifting; it’s always a moving target," he says. "You can’t triangulate a winning piece of art because there aren’t three points to lock it down in space."

Of course, Daigh’s pushpin portraiture is about as close as you can get to a winning formula in the art world. Maybe that’s why Daigh is throwing himself back into the realm of the unknown, working on new, avant garde approaches that will challenge the very meaning of a portrait. The first is essentially a television that sits on your wall, but it’s curated, 24/7, by content Daigh wants you to see—forming a sort of self-portrait of his own consciousness. In his other artistic tangent, Daigh is drafting portraits as complex, 3-D rooms. He’s creating virtual architecture to embody someone.

And notably, neither project would have been possible for his father to create before that first Mac.

"There was a time when I wanted to make work that was less computer-driven, then it occurred to me, why am I apologizing for this?" he says. "When I came into art, that was how you did it. With computers. I came at the beginning of that revolution. I realized it was time to stop apologizing for not drawing things."

As odd as these approaches may sound now, to Daigh, it fit perfectly into his style. Not only are they all computer-generated; they’re all, ultimately, just images of people. "As much as I try to come up with something different, I don’t know how much more interesting anything else could be to me than portraiture," he says.

"You mean, capturing the very essence of humanity?" I ask. "The physical manifestation of someone’s very psyche?"

This is awesome, but I don't envy him. I bet he's raking in the $$$ and getting excellent recognition for his work - but the majority of the actual hours he spends working must be spent doing formulaic and procedural stuff. I wonder if he ever misses the old days?

Or if he's considered doing the Renaissance artist trick, hiring an assistant to actually put in the pins? Though I imagine that would destroy the magic...